[RefactorCareer]

I thought money and flexibility would be enough, but working on simple client requests is boring me to death, and I miss the ownership of working on a product. I'm sure I could milk this out until I retired, but there are other issues with the company, and I don't want to be miserable at something that takes so much of my day.

[pjmorris]

I've found the principle 'Run toward things, not away from things' to be helpful. If you don't know what'll really make you happy, you've got a shot at winding up just like you are now, somewhere else.

Finding, or starting, a relevant project, using technology you want to emphasize, seems to me like a step you could take independent of what you do about the job. As for the job, I think what they say about 'Change your organization, or change your organization' is true.

Of course, in similar shoes, I did something radical. I wasn't fulfilled in my monied, flexible job, so I'm taking a leap at what I really want to do: teach in college. It started when I came home from work one day, with a plan for how I could help local high schools with their AP classes and computer clubs, and my wife asked whether that would really do the trick of making me happy. I said 'No' and, 4 years later,I'm now ABD on a PhD, and could tell long stories of the highs and lows. It looks like it'll work out, but there's still a really strong case for having kept the boring job and looking for fulfillment elsewhere. Look up Eric Hoffer, who was a longshoreman by day, and philosopher and author by night.